Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

Khalil, Iman M.; Barker, David; Copp, Brent R.

doi:10.1021/acs.joc.5b02312

Cited by 27 publications

(13 citation statements)

References 28 publications

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“…NAK derivatives and analogues have shown their pharmaceutically importance in scavenging of free radicals and prevention of protein destruction as antioxidant (Ressmeyer et al 2003) and neural nitric oxide synthase inhibitor (Entrena et al 2005). NAK was also a versatile organic synthetic building block in the chemical synthesis of some biological active alkaloids (Khalil et al 2016;Skyler and Heathcock 2001). In this work, a 28 mg L −1 of NAK could be obtained from the biotransformation of tryptamine in the C. acuminata cell suspension cultures, which is an alternative biological preparation of NAK.…”

Section: Discussionmentioning

confidence: 99%

Enhanced production of camptothecin and biological preparation of N 1-acetylkynuramine in Camptotheca acuminata cell suspension cultures

Yang

Xiang

Xing

et al. 2017

Appl Microbiol Biotechnol

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The Camptotheca acuminata cell suspension cultures were established to produce the well-known antitumor monoterpene indole alkaloid camptothecin (CAM). Most CAM was present in the broth of the C. acuminata cell suspension cultures. The CAM production was evidenced to be attenuated when the C. acuminata cell suspension cultures were continuously subcultured and grown under identical axenic conditions. A practical cryopreservation and recovery procedure was established to maintain the C. acuminata cell suspension cultures. Biotic and abiotic elicitors were administrated to the C. acuminata cell suspension cultures to restore and enhance CAM production. Of them, sorbitol, a well-known hyperosmotic stressor, was proven to be the most effective elicitor that stimulates a ∼500-fold increase of CAM production. The committed biosynthetic precursors of CAM, tryptamine and secologanin, were feed to the C. acuminata cell suspension cultures and the CAM production is not remarkably increased. However, N 1 -acetylkynuramine (NAK), an important metabolite of kynuramine pathway, was isolated and identified from the cell suspension cultures feeding with tryptamine. The present work provides an efficient method to produce CAM and NAK using the C. acuminata cell suspension cultures. The biotransformation of tryptamine to NAK sheds lights on the biosynthetic formation of the pyrroloquinoline moiety of CAM.

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Section: Discussionmentioning

confidence: 99%

Enhanced production of camptothecin and biological preparation of N 1-acetylkynuramine in Camptotheca acuminata cell suspension cultures

Yang

Xiang

Xing

et al. 2017

Appl Microbiol Biotechnol

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“…Both two types of pyridoacridine alkaloids have received enormous attentions due to the unique biological properties and many efforts have been devoted to construct these pyridoacridine frameworks, involving condensation of amino‐ketone substrates, [ 4 ] cyclization of anionic nucleophilic addition, [ 5 ] electrocyclic ring closure, [ 6 ] Cadogan reaction [ 7 ] and biomimetic cascade reaction. [ 8 ] However, these methods suffered from the drawbacks such as use of harsh conditions, prolonged reaction times and especially the narrow substrate scopes and they could not be applied in different ring systems. Accordingly, for further screening biological evaluation, the development of a divergent and efficient access for both pyrido[2,3,4‐ kl ]acridine and pyrido[4,3,2‐ kl ]acridine analogues is still of great interest.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Divergent Syntheses of Pyridoacridine Alkaloids viaPalladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes

et al. 2021

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Main observation and conclusion A divergent and novel protocol for the preparation of both pyrido[2,3,4‐kl]acridine and pyrido[4,3,2‐kl]acridine alkaloids was developed. This method featured the remote palladium‐catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been successfully applied to the total synthesis of norsegoline, styelsamine C and the skeleton of necatorone.

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“…Synthesis of the protected compounds followed general procedures outlined in the existing literature, as stated more fully in the Supporting Information. [14][15][16][17][18] Acetyl, p-tosyl, and methoxycarbonyl drug derivatives were isolated by liquid-liquid extraction, and TLC after concentration in vacuo showed only one spot. Fmoc and t-Boc drug derivatives required further purification and were isolated by column chromatography on silica gel.…”

Section: General Synthetic Procedures (Figure 1)mentioning

confidence: 99%

Identification and characterization of chemically masked derivatives of pseudoephedrine, ephedrine, methamphetamine, and MDMA

Mayer

Copp

Bogun

et al. 2020

Drug Testing and Analysis

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The emergence of chemically masked illicit drugs represents a challenge to global initiatives that are working to prevent their manufacture and distribution. Targeted analytical techniques currently used by law enforcement to identify unknown materials rely on spectroscopic and spectrophotometric databases that do not currently include some of these compounds, making their identification challenging. This study aimed to update compound spectral libraries to aid in the rapid detection and identification of these masked drugs, as well as to provide insight into their synthetic procedures. Five commonly employed protecting groups, acetyl, p‐tosyl, methoxycarbonyl, Fmoc, and t‐Boc, were appended to pseudoephedrine, ephedrine, methamphetamine, and MDMA. Characterization was carried out using NMR, GC‐MS, FTIR, high‐resolution LC‐MS/MS, and common screening color tests. Some of the methoxycarbonyl and t‐Boc derivatives and all of the Fmoc derivatives showed partial or full thermal degradation or rearrangement during GC‐MS analysis, while LC‐MS/MS analysis did not always show characteristic fragmentation that would allow unambiguous assignment of the structure. Restricted rotation in some of the derivatives meant that NMR assignments could only be made using NMR spectra acquired at elevated temperature. Therefore, GC‐MS and LC‐MS/MS analyses serve complementary roles for these derivatives, with NMR providing confirmation of structure for the pure materials if necessary.

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Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

Cited by 27 publications

References 28 publications

Enhanced production of camptothecin and biological preparation of N 1-acetylkynuramine in Camptotheca acuminata cell suspension cultures

Enhanced production of camptothecin and biological preparation of N 1-acetylkynuramine in Camptotheca acuminata cell suspension cultures

Divergent Syntheses of Pyridoacridine Alkaloids viaPalladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes

Identification and characterization of chemically masked derivatives of pseudoephedrine, ephedrine, methamphetamine, and MDMA

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